Benzindene prostaglandins. Synthesis of optically pure 15-deoxy-U-68,215 and its enantiomer via a modified intramolecular Wadsworth-Emmons-Wittig reaction

…, PA Aristoff, PD Johnson, JP McGrath…

Index: Lin; Aristoff; Johnson; McGrath; Timko; Robert Journal of Organic Chemistry, 1987 , vol. 52, # 25 p. 5594 - 5601

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Citation Number: 16

Abstract

The optically pure [[1 (R)-(3-cyclohexylpropyl)-2, 3, 3a, 4, 9, 9a-hexahydro-2 (R)-hydroxy- (3aS, 9~)-l~-benz~-inden-5-yl] oxy] acetic acid (2a) and its 1, 2, 3a, 9a-tetraepi isomer (2b), 15-deoxy analogues (prostaglandin numbering) of the potent antiulcer agent 1 (U-68,215), have been synthesized. The resolution of the optical isomers was accomplished by LC (liquid chromatography) separation of the 2 (RS)-(S)-a-methylbenzyl carbamates 8a, b, ...